Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work – investigating, resolving, and acting on every signal across every channel that matters.
Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself.
We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io http://Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List https://www.enterprisetech30.com/.
What You’ll Do 📌
- Build the function. This is our first San Francisco based SDR leadership hire. We have basic playbooks, messaging, and sequences that already work — you'll sharpen them, fill the gaps, and build the rest (process, tooling, cadences, ramp plan) as you scale the team.
- Hire and build the team. Recruit, interview, and hire a team of SDRs. You'll own headcount planning and be the primary driver of who joins the team.
- Coach and develop. Run 1:1s, call reviews, and pipeline reviews. Train reps on prospecting, messaging, and objection handling. You'll be evaluated on how well your reps improve under you, not just on their output.
- Own team quota. You're held to your team's outbound pipeline targets — meetings booked, opportunities created, and pipeline generated across the team. You won't be booking meetings yourself, but you're accountable for the number.
- Manage performance. Set expectations, track individual and team metrics, and manage performance issues directly, including coaching underperformers and making tough calls when needed.
- Partner cross-functionally. Work closely with AEs on messaging, handoff quality, and feedback loops. Partner with marketing on targeting and campaigns. Report directly to our founder, who leads GTM.
- Own the target account strategy. Set the criteria and direction for account selection (150-1000 employees) and ensure the team is prospecting the right accounts, even though you're not building lists yourself day-to-day.
Who You Are 💼
- 2+ years managing an SDR team, ideally at an early-stage startup — required.
- You've hired for and grown a team before, not just inherited one.
- Track record of your team hitting or exceeding pipeline/quota targets — you know how to build a number and hold people to it.
- You can coach: you know how to diagnose why a rep isn't converting and fix it, not just tell them to dial more.
- You've built or meaningfully shaped an outbound motion before — process, messaging, sequencing — even if you're not building from a blank page here.
- Experienced with a modern sales stack (SFDC, Amplemarket or similar engagement tools) and comfortable using data to run the team.
- Strong communicator who can operate with real autonomy — this isn't a hand-holding environment, and you'll have a direct line to our founder.
- (Bonus) Experience selling or managing a team that sold into support / CS / post-sales personas.
Our Perks
🏥 Fully covered medical, dental, and vision insurance for employees
🏦 401(k) retirement plan
🚆 Commuter benefits
🌱 Parental leave
🏝️ 14 company holidays + unlimited PTO
🗺️ Annual offsite
🍽 Lunch, dinner, and snacks at the office
🏋️ Fitness stipend
More about Pylon
Traction: Have 1300+ customers and growing fast
Funding: Series B led by a16z and BCV ($51M total raised)
Founders: Advith Chelikani https://www.linkedin.com/in/advith/, Robert Eng https://www.linkedin.com/in/robert-eng/, and Marty Kausas https://www.linkedin.com/in/martykausas
Team: Currently 110 and growing!